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N-(Benzyloxycarbonyloxy)succinimide

ALDRICH/227781 - 98%

Synonym: Benzyl N-succinimidyl carbonate; Z-OSu

CAS Number: 13139-17-8
Empirical Formula (Hill Notation): C12H11NO5
Molecular Weight: 249.22
EC Number: 236-075-3
MDL Number: MFCD00005513
Linear Formula: C12H11NO5
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-227781-25G 25 g
 $115.00
1/EA		 Add To Favorites
45-227781-100G 100 g
 $191.00
1/EA		 Add To Favorites
45-227781-250G 250 g
 $206.00
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This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material.

This image depicts SKU: 227781-100G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material.

This image depicts SKU: 227781-250G

 

application(s) peptide synthesis
assay 98%
functional group imide
  phenyl
InChI 1S/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2
InChI key MJSHDCCLFGOEIK-UHFFFAOYSA-N
mp 80-82 °C (lit.)
Quality Level 200 
SMILES string O=C(OCc1ccccc1)ON2C(=O)CCC2=O
Application: N-(Benzyloxycarbonyloxy)succinimide (Cbz-OSu) is a common reagent for the carboxybenzyl protection of amines. This reaction is one of the key synthetic steps in the synthesis of:
• Enantiomers of cyclic methionine analogs viz, (R)-and (S)-3-aminotetrahydrothiophene- 3-carboxylic acid.
• 1′-H-Spiro-(indoline-3,4′-piperidine) and its derivatives.
• Total synthesis of (-)-diazonamide A. and (-)-sanglifehrin A.

Cbz-OSu is widely employed to protect amino acid residues in peptide synthesis. It can also be used in N-trans diprotection of cyclen regioselectively.
Application: Reagent for the selective introduction of the Z-amino protection in amino acids; and in aminoglycoside antibiotics.
Packaging: 25, 100, 250 g in poly bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity 98%
mp 80-82 °C (lit.)
UNSPSC 12352005

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